Angelina Jolie dating history reveals a complex and highly publicized journey involving several key relationships from her early career until present day. Over nearly four decades as a celebrated actress, humanitarian, and mother, Jolie’s romantic life has attracted significant attention, particularly her connections with actors Jonny Lee Miller, Billy Bob Thornton, Brad Pitt, and rumored links to Val Kilmer.
While Jolie is currently single and focused on her family and personal pursuits, her past includes two marriages, a notable decade-long partnership with Brad Pitt, and an exploration of her identity that was publicly acknowledged. Below is an in-depth look at the major relationships that have shaped Angelina Jolie’s personal life over the years.
Early Marriage and Partnership with Jonny Lee Miller
Angelina Jolie first met British actor Jonny Lee Miller on the set of the 1995 film Hackers. Their connection quickly led to marriage in 1996, but the couple separated the following year. Jolie officially filed for divorce in 1999 amid a period of self-discovery.
Reflecting on that time, Jolie shared in a 1996 interview,
“It was weird to immediately be married, and then you kind of lose your identity. You’re suddenly somebody’s wife. And you’re like, ‘Oh, I’m half of a couple now. I’ve lost me.’ We went on some morning show, and they threw rice on us, and they gave us toasters. I was thinking, ‘I need to get myself back.’”
– Angelina Jolie, Actress
Despite their separation, the two have maintained a positive relationship. Jolie expressed in 2025 during a Q&A session at the Santa Barbara International Film Festival,
Image of: Angelina Jolie
“I do have a wonderful relationship with Jonny. He and I have sons the same age, and I’m so happy.”
– Angelina Jolie, Actress
Relationship with Model Jenny Shimizu and Sexual Identity
Angelina Jolie’s relationship with model Jenny Shimizu began after they met while filming the 1996 drama Foxfire. Though the exact duration is not fully documented, Jolie openly spoke about her deep feelings and evolving understanding of her sexuality during this period.
In a 1997 interview with Girlfriends magazine, Jolie acknowledged the intensity of her connection with Shimizu, stating,
“I probably would have married Jenny Shimizu if I hadn’t married my husband. I fell in love with her the first second I saw her.”
– Angelina Jolie, Actress
Jolie also reflected on how Jonny Lee Miller supported her journey of self-discovery, saying,
“He was around when I was figuring things out about myself, when I was realizing that I was attracted to women also,”
and added,
“If anything, he took it very seriously. When I realized that somebody like Jenny could be a deep love for me, he realized it, and he took it very seriously.”
– Angelina Jolie, Actress
Marriage to Billy Bob Thornton
Angelina Jolie met actor Billy Bob Thornton while filming Pushing Tin in 1999. Though Thornton was reportedly engaged elsewhere at the time, he and Jolie eloped in Las Vegas in 2000. Their marriage overlapped with Jolie’s decision to adopt her first son, Maddox, in 2002.
The couple separated later that year, and their divorce was finalized in 2003. Despite the split, Thornton has spoken fondly about their time together. In a 2025 interview with Rolling Stone, he remarked,
“We simply split up because our lifestyles were so different.”
– Billy Bob Thornton, Actor
He further reflected on their shared experiences, saying the relationship was
“one of the greatest times of my life.”
and added,
“She and I are still very, very close friends.”
– Billy Bob Thornton, Actor
Speculated Romance with Val Kilmer
Angelina Jolie worked alongside Val Kilmer in the 2004 historical drama Alexander, prompting speculation about a brief romance between them. Although neither confirmed a relationship at the time, Kilmer expressed admiration for Jolie in his memoir I’m Your Huckleberry.
He wrote,
“I couldn’t wait to kiss Angie, buy her a Gulfstream jet, and have a V+J painted in rainbow glory on the tail,”
as reported by Us Weekly. Kilmer also described Jolie’s unique qualities, stating,
“When people ask me what Angelina is like, I always say she’s like other women and other superstars but just more,”
continuing,
“More gorgeous. More wise. More tragic. More magic. More grounded.”
– Val Kilmer, Actor
No public confirmation of a relationship between Jolie and Kilmer ever emerged.
Long-Term Partnership and Marriage to Brad Pitt
Angelina Jolie’s most high-profile and extended relationship was with Brad Pitt. The two met during the filming of Mr. and Mrs. Smith in 2003 when Pitt was still married to Jennifer Aniston. Their relationship became public in early 2005 following Pitt’s separation from Aniston.
In April 2005, Jolie and Pitt were seen traveling to Kenya with Maddox, Jolie’s adopted son, what confirmed their partnership. Together, they built a family of six children: Maddox; Zahara, adopted in 2005; Shiloh, born 2006; Pax, adopted in 2007; and twins Knox and Vivienne, born in 2008.
The couple announced their engagement in 2012, with Pitt’s manager telling People magazine,
“It is a promise for the future, and their kids are very happy.”
– Brad Pitt’s Manager
They married in 2014 at their estate in France, Château Miraval. However, Jolie filed for divorce in 2016, initiating an extended and highly publicized separation process. Reflecting on the decision, Jolie told The Guardian in 2021,
“It took a lot for me to be in a position where I felt I had to separate from the father of my children.”
– Angelina Jolie, Actress
The divorce was finalized in 2024, with Jolie’s attorney stating to CNN,
“Frankly, Angelina is exhausted, but she is relieved this one part is over.”
– Angelina Jolie’s Attorney
Legacy and Current Status in Jolie’s Romantic Life
Angelina Jolie’s dating history reflects a path marked by intense relationships, personal exploration, and public scrutiny. Her journeys with loved ones like Jonny Lee Miller, Jenny Shimizu, Billy Bob Thornton, Val Kilmer, and Brad Pitt cast light on her complex emotional landscape and evolving self-awareness.
Now publicly single, Jolie continues to prioritize her family and professional endeavors, carrying the experiences of her past relationships into her current life. Her story remains a testament to resilience and candid self-expression amid the pressures of fame.
BREAKING: Angelina Jolie and Brad Pitt were married Saturday in France, says a spokesman for the couple.
